In Love with a Bad Boy
by livvy180599
Summary: Blair falls hard for our resident bad boy!
1. Chapter 1

Chuck's POV

I stepped into Blair's residence and the immediate stench of alcohol and teenage desperation filled my senses. I walk across the lobby and into the main party room. I spot Serena, Nate, Dan and Vanessa, all sitting at the bar. I start to walk over to the other side of the room and when I approach the four of them, I hear those dreaded words.

"Blair's upset"

"What's the matter?" I ask them worriedly.

"Oh, hey Chuck, I was just telling them how Blair locked herself in her room, hey, maybe you could talk to her, she won't listen to us" Serena states.

"As if she would listen to Chuck" Dan laughs. I roll my eyes at him. **Jerk!**

"I'll try" I say walking towards Blair's bedroom.

I knock on the door and hear soft sniffles. I frown and open the door.

"B, you okay?" I ask slowly closing the door behind me.

"Not really" she replies sitting on the end of the bed.

"What's the matter?" I ask her moving to sit next to her on the bed.

"Well I see everyone being coupley and I can't help but think that I'm not going to have that. On top of that I'm alone on my birthday, so I have no one to kiss for my wish" She replies resting her head on my shoulder.

"You're not alone, B, you have us" I say back.

"I know, but who can I kiss for my birthday wish?" she asks me.

"You can kiss me" I say quietly. I feel Blair lift her head up off my shoulder and look at me.

"What?" she asks quietly. I sighed before answering.

"I love you Blair" I say softly looking into her beautiful eyes.

"No, don't play with me like that" she replies resting her head back on my shoulder.

"I'm serious Blair, I've loved you since seventh grade, but I could never have you, because you were dating Nate" I explain.

"I never knew you felt that way" she states looking at me again.

"Yeah, well, I kept it pretty hidden behind all the alcohol, drugs and one night stands" I say.

I felt Blair take hold of my face and turn my head to face her.

"I love you too Chuck, although only since eighth grade." She giggles before attaching her lips to mine.

The kiss started off slow and sweet but eventually became more heated. I felt Blair start to push me back onto the bed and I unwillingly stopped her.

"Blair, stop" I say regrettably.

"What's wrong?" she asks worriedly.

"Nothing, I just don't want to rush into things. I want to prove to you that I really love you" I say whole heartedly.

"Okay, just promise me one thing?" she says looking down at our intertwined hands. I nodded looking straight at her.

"Promise me, you'll give up other women for me?" she asks with a pleading look. I smile at her and nod slightly.

"In a heartbeat" I reply and she kisses me tenderly again.

"We should probably go out there before they come looking for us, but I think that we should keep this as our little secret, wouldn't want Gossip Girl to find out" I say smirking.

"I totally agree" she says before moving off my lap, pecking my lips in the process. We both straighten out our clothes before we leave her bedroom and walk back downstairs. When we reach the others, we look at each other with a look that says 'Acting time'.

"Blair are you alright?" Serena asks hugging her best friend.

"Yeah, I just had a breakdown, it's all good now" Blair replies sneaking a glance at me. **This is going to be fun.**


	2. Chapter 2

Two weeks later Serena's POV

I was talking with Nate, Dan, Jenny and Vanessa when a Gossip Girl blast came out. Everyone looked to their phones and gasps were heard.

 _Listen up, upper east siders, this just in. B and C were spotted getting 'Frisky' behind the school. Don't believe me, see for yourself._

A video started to play and I gasped again, I look at the others and they were shocked too.

"Oh, my God, that's Blair" Jenny states.

"Who's the guy?" Dan asks.

"I have no idea" I say as Blair walked up to us.

"I hate Gossip Girl" she says angrily. "Before you ask, I'm not going to tell you who the guy is"

As she walks off I can see her heading towards Chuck.

"Has anyone else noticed that Blair and Chuck are always around each other, or the fact that she has her hands in his hair right now" I say shocked as everyone else turned around to look at them.

"Now that you mention it, I've caught Blair staring at Chuck a couple of times, but I never asked her about it" Jenny says.

"You don't think…" Dan starts before I interrupt.

"Let's follow them"

We followed Blair and Chuck through the school courtyard to the back gate.

"Where are they going?" Nate asks confused.

Our school is located next to a cemetery and that is exactly where we are headed. The two of them stop in front of a grave and we watch as Chuck falls to his knees. By doing so I found the name on the gravestone.

 _Laura Annalise Bass_

 _A loving wife and daughter_

My heart sank as I watched Blair kneel down on the dirty grass next to Chuck. She'd never intentionally get dirty if it wasn't important. It was a couple of minutes before anyone spoke.

"It's not your fault you know that" I hear Blair tell Chuck.

"I know, but I feel as though it was" Chuck says quietly. **I've never seen him so vulnerable.**

"Chuck, look at me" Blair says sitting in front of him.

Chuck looked up at her and she smiled warmly.

"Listen, if you're ever feeling like this or your father says something, just call me, I'll drop everything to be there for you" she says.

"Why?" Chuck asks her.

"Because I love you" she states softly. All of our eyes become wide as we watch Blair kiss Chuck.

"Oh my god, Chuck's the guy in the video" Jenny whispers.

"That's surprising, I didn't even know they were that close" Dan says.

"They've always been close, they just don't show it to others" I say smiling slightly.

"Then, why hide the fact that they are close from everyone?" Jenny asks.

"Because of their labels, they are supposed to hate each other, even as kids they were always closer than everyone else" I say.

"What happened to Chuck's mum?" Dan asks.

"She died during childbirth. Chuck's father blames Chuck for her death" Nate says "I never realized just how much Chuck blames himself until now"

"Is this where he goes every lunchtime?" Dan asks.

"I guess" I reply.

We watch as Blair and Chuck stood up from the ground, dusted themselves off and started walking back to the school. We followed behind them slowly as to not alert them that they were being followed.

"We should probably not tell anyone what we saw" Jenny says.

Agrees were heard around the group. When we arrive back at school, we watched as Chuck pulled Blair into a kiss. Blair's hands found their way into his hair while Chuck's found her waist. They pull away a few seconds later and Chuck whispers something in her ear and she smiles.

"I know" she replies before Chuck walks around the corner.

"Believe me, I know" she breathes before walking out from behind the corner.

"What just happened?" Nate asks.

"I have no idea" **Their guess was as good as mine!**

We walked back around the corner into the school courtyard to go to class.


	3. Chapter 3

Later that Day at Blair's house, Serena's POV

We were supposed to be getting ready for our family dinner, well my family dinner that involves Chuck too. I invited Dan, Nate, Blair and Jenny there for support, which Chuck was fully supportive of. But apparently Blair's to busy texting someone, Chuck, I'm guessing. I grabbed a pillow and pivoted it at her head.

"Hey, why did you do that?" she asks angrily.

"Stop sexting Chuck" I smirk.

I see her face turn bright red and I laughed.

"No, I'm not gross, why would you even say that?" she stutters nervously.

 **Okay then!** I sighed and went for it.

"B, I know, you're hooking up with Chuck, I saw you at the back of the school today" I say laughing at her shocked expression.

"Please, don't tell anyone, Serena, we aren't ready to tell everyone yet" she begs me.

"I won't, just don't let me catch you hooking up" I say grimacing.

"Don't worry, that won't be a problem" she says sadly. I frowned.

"Haven't you done it?" I ask quietly.

"No" she replies "he wants to wait.

"Chuck, wants to wait, are you serious?" up exclaim shocked.

"He says he wants to prove to me that he loves me, but I already know he does" she replies.

"So tell him, you know it" I say.

"I have, but he won't respond to any of my advances" she states clearly frustrated.

"Well, we'll just have to make him respond" I say smirking.

"How are we going to do that?" she asks me innocently. I frown again.

"B, have you ever seduced a guy before?" I ask her.

"No"

"Have you actually done it?" I ask already knowing the answer.

"No" she says quietly.

"Oh, I have so much to teach you" I exclaim overdramatically.

"Shut up" she laughs blushing.

"First things first, you have to have a killer outfit" I start as I walk over to the closet. I pull out a long emerald lace dress with a slit up the leg.

"Sexy, yet elegant"

While she studied the dress I went over to her underwear drawer. I pulled out a matching black lace set and sat it on the bed. I threw a pair of lacy thigh high stockings and a pair of black heels at her as well.

"Go get dressed" I say pushing her into the bathroom.

While she got dresses, I did as well. When she came out, she looked like a goddess.

"Wow" I exclaim wide eyed.

"What wrong?" she panics.

"Nothing, you just look so hot right now, Chuck will be all over you by the end of the night. And by the way, the there's don't know, and maybe bring him back here, so the rest of us don't have to listen" I tease.

She smirks right back at me before her expression becomes worried.

"Does it hurt?" she asks worriedly.

"Only at first, but as long as you tell Chuck it's your first time, he'll be gentle, I know that for sure, he loves you Blair" I reassure her.

"Let's go" she says grabbing my arm and her purse.


	4. Chapter 4

At the restaurant Blair's POV

Serena and I walked in to find everyone already at our table. I saw Chuck's eyes widen and his jaw tighten. He pulled out my chair for me, like the Gentleman he was. I looked at Serena and she winked at me. I quietly sent a text to Serena.

B: What do I do know?

S: Seduce him!

B: How?

S: Maybe, flirt with him a little, I'll distract everyone else.

Serena starts talking to Jenny, Nate and Dan. Before I could start a conversation with Chuck, I received another message from Serena.

S: Touch his thigh

B: What?

S: Lightly rest your hand on his thigh!

I rested my hand on his thigh and I felt him tense up before slowly and quietly releasing a breath. I smirked slightly and took a chance. I moved my hand further up his thigh and I felt him grab my wrist, pulling my hand away. I frowned at Serena and I saw her give a confused look back.

S: Don't worry B, he'll 'come' around soon ;)

B: Gross

"Blair, is something wrong?" Lily asked me.

"No, not at all why?" I ask confused.

"It's just that you keep glaring at your phone" she replies.

I smile sheepishly as my phone buzzed again.

S: Sexually frustrated huh? J

B: Shut up!


	5. Chapter 5

After our dinner, we all headed out into the streets to get in our cars (Or limos!)

"Well, we better go" Dan says walking to his car with Jenny. After saying goodbye, I realized something.

"S, Dan brought me here, how am I meant to get home?" I ask panicking.

"Charles will take you home" Bart said.

Chuck opened the door for me as I got in. my heart fluttered and I had to stop myself from smiling.

"There, you go, problem solved" Serena says with a smirk "Have fun"

She winks at me slyly. **She planned this. Bitch!**

"What was that about?" Chuck asks after sliding in behind me, shutting the door in the process.

"She knows about us" I blurt out.

I see his eyes go wide.

"Look, I know you love me, okay, you have proved that to me, now get over here before I change my mind about giving my virginity to you" I say as seductively as I could master. It obviously worked because within a minute, Chuck's lips were on mine and he had his hands on my waist. I thread my hands through his hair and heard him moan when I dug my nails into his scalp. I smirked victoriously and moved to straddle his lap.

"We have arrived" a voice said from the front seat. I heard chuck groan as an idea came to me. I got out of the limo dragging Chuck out with me.

"Hey, Anthony, take the rest of the night off okay? Mr Bass is staying here" I say before pulling Chuck towards the elevator. On the way up to my apartment, I could feel the sexual tension between us. I couldn't take it anymore and attached my lips back onto his. I heard the elevator ding, but we never released our hold on each other. As we stumbled through the elevator door, I heard Dorota approach us.

"Miss Blair, I hear stumbling, you okay?" she asks wordily.

"Yes, Dorota, I'm fine, Chuck was just walking me in" I giggle as Chuck attacks my neck with his lips.

I watch her eyes go wide as she realizes my intentions.

"Miss Eleanor, away" She says before walking away, winking at me.

I giggle again and grab Chuck's hand, leading him up the stairs. Once up the stairs, I attack Chuck's lips again and he pushes me against the door. I gasp as he attaches his lips to my neck. I push him away slightly so I could wrap my legs around his waist. He walks over to the bed and we fall onto it. **Let's just say that losing my virginity was a pleasure, literally.**


	6. Chapter 6

I felt the sun warming up my bare back as I woke up and I smiled. The events of last night came flooding back to me, I reached over and slide my hand down Chuck's toned Chest. I hear him groan as he regains consciousness.

"Morning" I say rolling over on top of him. I sigh at the direct contact.

"It is a good morning" he says huskily. **Fuck, I thought his normal voice was hot!**

I leaned down to kiss him just to have his lips connect to mine first. I slide my tongue into his mouth as his hands find their way to my butt.

"Miss Blair, Miss Serena is here" I hear Dorota yell up the stairs.

I pull away and Chuck groans while I giggle at him.

"Go shower, there's things in the back of the closet for you" I say as I quickly get dressed and look presentable. He has many clothes that stay here after all the lights we fell asleep watching movies. Same as at his place. I walk down the stairs to find Serena smirking at me.

"So, how'd it go?" she asks, clearly already knowing the answer.

"It went great" I say unable to keep the smile off my face.

"Clearly" she smirks again.

"What are you doing here?" I ask looking back up the stairs.

"Well, I was coming to get you for school but I guess you were busy" she laughs.

"Yeah, I am" I say smirking back at her.


	7. Chapter 7

Later that day Serena's POV

"Has anyone seen Blair?" I ask sitting down at the table.

"Yeah, she's in the bathroom" Jenny says.

"Really?" I ask.

"Yeah, why?" Nate asks me.

"Because she went to the bathroom twenty minutes ago" I say.

"What's the bet that Chuck's in there too" Nate laughs.

"No bet" I say as Chuck walks up to the table from St Jude's.

"Hey, Chuck, have you seen Blair?" Jenny asks.

"Not since this morning why?" he asks.

"Just asking"

Next day Blair's POV

I walk over to our table and sit down.

"Blair, where were you yesterday?" Serena asks me.

"I went home, I had the flu" I say sadly.

"Aww, you poor thing" she says hugging me.

"Chuck's out sick with the flu too" Nate states.

"Really, it must be going around?" I half lie, looking down at the metal table.

"Blair, we know about you and Chuck" Nate states chuckling.

I feel my face go red and I avoid eye contact.

"Why didn't you tell us?" Dan asks.

"Oh, year, cause that would work, hey guys, guess what, I got an A on my assignment, Chuck and I are dating, How about sushi for Lunch?" I say sarcastically.

"You don't put it that way, but we would have been okay with it" Serna says.

"Really, you would have been alright with it?" I ask looking at Nate.

"Look, it would take some getting used to, but if u managed to capture, the heart of Chuck Bass, then it must be special" he says as the rest of us laugh.

"Really?" I ask looking at the rest of the group.

"Yeah, you and Chuck have been best friends since you were little, it was bound to happen eventually" Serena exclaims.

"You know, you must be special" Nate states.

"Why?" I ask worriedly.

"Because, Chuck doesn't go near sick people and I know you gave him the flu"

"Well, that was his own fault, he should have just left me in misery" I say overdramatically.

"Blair, you know he wouldn't do that, you know that when Chuck cares about something, he'll do anything for it that includes you" Serena says.

"Yeah, he'll be back tomorrow, it was only an overnight flu" I say smiling.

That afternoon. Serena's POV

"Hey, Nate, how's Chuck doing?" I ask walking to the front door.

"I don't know, we only just got here" he replies walking towards Chuck's door.

I lift my hand to knock when we hear Laughter. Dan, Jenny, Nate and I all look at each other.

"No, STOP, NO, NOT THERE, HAHA" a female voice says.

I raise my fist and knock twice on the door. Within a few seconds the door opened to reveal a flushed face Blair with a large smile on her face.

"Hey guys, what you are doing here?" she asks opening the door wider to let us in.

"We came to see Chuck. Where is he?" Dan asks.

"Sleeping" she simply states walking over to the plush sofa and sitting down.

"Then why were you laughing like a maniac?" I ask smirking at her.

"Because of this little guy" she says picking up a small puppy from behind her.

"Omg, that's adorable" Jenny says sitting next to Blair on the couch and holding the small puppy.

"B, do you have a hair clip I could use?" I ask her smiling at the small puppy situated in Jenny's lap.

"Yeah, I'll just get it for you" she says walking into the bedroom.

"I've never seen her happier than when she is with Chuck" I whisper not wanting Blair to hear.

"They really must mean a lot to each other" Nate replies smiling.

"Here you go, S" Blair says walking back into the room, handing me the clip.

"Thanks" I say as I place it in my thick hair, holding it up.

"Does anyone want a drink?" she asks walking over to the bar.

"I would" I say as everyone else agrees.

In a couple of minutes Blair returned with four glasses and handed them to us.

"So what's going on?" she asks sitting down on the couch next to me.

"Well, honestly we were just talking about how much happier you look since you've been with Chuck" I say smirking.

"What?" she asks quietly.

"Well for starters your eyes light up whenever you talk about him and your smile gets wider when you're around him" Nate says.

Blair breaks out into a small smile.

"You really love him, don't you?" I ask as she looks at me with so much love in her eyes.

"Yeah, I have ever since eighth grade" she admits shyly.

"Eighth grade, Blair why didn't you do anything about that then" Nate says shocked.

"Because, Chuck Bass doesn't do girlfriends" she states.

"Well, that's obviously not the case now" I say giggling.

"How long has this been going on?" Dan asks.

"About two weeks" she says smiling.

"Hey, Guys" a voice says from behind us.

"Chuck, hey, how are you feeling?" Nate asks as we all turn around to look at the voice.

"Better, what are you all doing here?" he asks clearly confused as to why a group of people were suddenly in his living room.

"We just wanted to make sure you were okay" Jenny chimes in.

He just nods and walks over to the kitchen. He grabs a glass of water and returns back to the sofa, taking a seat next to Blair.


End file.
